This invention relates to the electrosynthesis of cyclic alcohols.
Cyclic alcohols are useful solvents. They are particularly useful as solvents for pharmaceuticals.
1,4-Dioxanol has been produced by mixing water and dioxane then adding hydrogen peroxide and ferrous sulfate. Tatsuya Shono et al., Nippon Kagaku Zasshi, "Radical Reactions of Organic Compounds with Fenton Reagent", 81(8) (1960) pp. 1344-1346 (translation).
1,4-Dioxanol has also been prepared by adding chloro-1,4-dioxane to a water suspension of sodium bicarbonate. N. V. Kunetsov and I. I. Krasavtsev, Dopov. Akad. Nauk. Urk. RSR, "Dioxin and its Reactions", Ser. B, 31(11) (1969) pp. 1016-1018. (Translation p. 6).
1,4-Dioxanol is also taught to be one of numerous photolysis products of dioxane. John J. Houser and Barbara A. Sibbio, Journal of Organic Chemistry, "Liquid Phase Photolysis of Dioxane", 42(12) (1977) pp. 2145-2151.
1,4-Dioxanol has also been identified as a by-product of a toxicity study for ethylene oxide. Hiderau Shintani, Hiroshi Suzuki and Takuma Oba, Eisei Kagaku, "Qualitative and Quantitative Aspects of Ethylene Chlorohydrin, Ethylene Glycol and Other Reaction Products of Ethylene Oxide in Saline During the Prolonged Incubation", 27(5) (1981) pp. 285-295 (translation).
U.S. Pat. No. 3,399,215, column 2, lines 3-16, teaches that the dehydration of diethylene glycol to p-dioxanone is believed to proceed through an intermediate, 1,4-dioxanol. The reference also teaches that the dehydration of secondary alcohols is known to proceed faster than the dehydration of primary alcohols. Therefore, the intermediate 1,4-dioxanol is not isolated.
None of these processes produce 1,4-dioxanols from inexpensive raw materials in reasonable yields. It is therefore desirable to have a process for producing cyclic alcohols and cyclic ketones from inexpensive raw materials in relatively high yields.